(S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-tert-butoxycarbonylamino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester

Base Information

Chemical Name:(S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-tert-butoxycarbonylamino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester
CAS No.:192211-88-4
Molecular Formula:C₄₂H₆₆N₄O₁₂
Molecular Weight:819.006
Hs Code.:

(S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-tert-butoxycarbonylamino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester

Synonyms:(S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-tert-butoxycarbonylamino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester

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Chemical Property of (S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-tert-butoxycarbonylamino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester

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Technology Process of (S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-tert-butoxycarbonylamino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester

There total 23 articles about (S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-tert-butoxycarbonylamino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

: 192211-69-1
(2S,3R)-3-[(S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionyloxy]-2-tert-butoxycarbonylamino-butyric acid

: (4S,5R,13S,15S)-4-Hydroxy-5-isobutyl-15-isopropyl-13-methyl-1-oxa-6,11-diaza-cyclopentadecane-2,12,14-trione; hydrochloride

: 192211-88-4
(S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-tert-butoxycarbonylamino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester

Guidance literature:: With 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In dichloromethane; 0 deg C, 30 min; room temperature, 6 h;
DOI:10.1021/jo9623696

Reference yield:

: 23032-21-5
D-leucine methyl ester

: 192211-88-4
(S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-tert-butoxycarbonylamino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester

Guidance literature:: Multi-step reaction with 18 steps

1: 83 percent / AcOH, Na(OAc)3BH / 1,2-dichloro-ethane / 12 h

2: 87 percent / Et₃N / CH₂Cl₂ / Heating

3: 97 percent / H₂ / Pd/C / methanol; ethyl acetate / 3 h / 2068.6 Torr

4: 93 percent / Et₃N / CH₂Cl₂

5: 91 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 4 h / 0 °C

6: 67 percent / DCC / CH₂Cl₂ / 12 h / Ambient temperature

7: 1) LDA / 1) THF, -78 deg C, 1 h, 2) THF, -78 deg C, 4 h

8: 78 percent / KBH₄ / ethanol / 0 deg C 1 h; ambient temperature, 24 h

9: 78 percent / 2,6-lutidine / CH₂Cl₂ / 6 h / 0 °C

10: 89 percent / aq. HOAc / tetrahydrofuran / 16 h

11: 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 0.5 h

12: aq. KMnO₄, NaH₂PO₄ / 2-methyl-propan-2-ol; diethyl ether / 1 h / 25 °C

13: 68 percent / DCC, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

14: 58 percent / 4-pyrrolidinopyridine, cyclohexene / Pd/C / dioxane; ethanol / 95 deg C, 1.5 h; 95 deg C -> 25 deg C, 48 h

15: 77 percent / Me₂BBr / CH₂Cl₂ / 1 h / -78 °C

16: 99 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 1 h / Ambient temperature

17: 90 percent / HCl(g) / ethyl acetate / -20 - -10 deg C, 2 h; 0 deg C, 4 h

18: 67 percent / BOP, NMM / CH₂Cl₂ / 0 deg C, 30 min; room temperature, 6 h

With 4-methyl-morpholine; 2,6-dimethylpyridine; hydrogenchloride; dmap; lithium hydroxide; potassium permanganate; sodium dihydrogenphosphate; potassium borohydride; dimethylboron bromide; hydrogen; sodium tris(acetoxy)borohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; 4-pyrrolidin-1-ylpyridine; acetic acid; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; cyclohexene; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; tert-butyl alcohol;
DOI:10.1021/jo9623696

Reference yield:

: 192211-84-0
(S)-2-(Benzyloxycarbonyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid methyl ester

: 192211-88-4
(S)-2-(Acetyl-methyl-amino)-3-(4-methoxy-phenyl)-propionic acid (1R,2S)-2-tert-butoxycarbonylamino-3-((4S,5R,13S,15S)-4-hydroxy-5-isobutyl-15-isopropyl-13-methyl-2,12,14-trioxo-1-oxa-6,11-diaza-cyclopentadec-6-yl)-1-methyl-3-oxo-propyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / H₂ / Pd/C / methanol; ethyl acetate / 3 h / 2068.6 Torr

2: 87 percent / Et₃N / CH₂Cl₂ / 12 h

3: 94 percent / aq. LiOH / tetrahydrofuran / 6 h

4: 82 percent / Et₃N, DMAP, isopropenyl chloroformate / CH₂Cl₂ / 1 h / 0 °C

5: 91 percent / H₂ / Pd/C / methanol; ethyl acetate / 3 h / 2068.6 Torr

6: 67 percent / BOP, NMM / CH₂Cl₂ / 0 deg C, 30 min; room temperature, 6 h

With 4-methyl-morpholine; dmap; lithium hydroxide; Isopropenyl chloroformate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1021/jo9623696